STYLE DILEMMA: What the Hell Do You Wear With Dressy Sweatpants?

"I need to know what to wear with a dressy pair of sweatpants," Emily recently asked me.

I feel like this is the defining style question of our generation. Okay, maybe that's an exaggeration — but don't tell me you haven't been noticing these fitted joggers in every store lately and wondering how to wear them.

Emily's dressy sweats are these sold-out Joe Fresh Jogger Pants. Below is a similar style from American Eagle.

Obviously, the easiest way to wear these is barefoot with a T-shirt around the house. But what if you actually want to wear these out of the house? How does one build an actual outfit around a pair of dressy sweats?

My best guess: through confidence and skillful subterfuge. You are wearing sweatpants in public. It's an unescapable fact. With the sudden popularity of these skinny joggers, however, it's not enough to simply want to be comfortable. You have to be stylish at the same time, which means you basically have to distract people from the fact that you are wearing sweatpants.

We shall accomplish this through the art of layering (and wearing shiny accessories).

I came up with three outfit ideas for Emily, based on the three occasions she might wear these joggers: weekends, casual dates or nights out, and work (yeah, I went there).

WEEKEND

First up, the ideal occasion for wearing these pants: casual weekend outings or events, like hanging out at the playground with her son or going to a get-together at a friend's place.

A red checked shirt makes a winter outfit more polished than a T-shirt. Wear it half-tucked with the sleeves pushed up to show off a few gold bracelets.

And instead of the dirty running shoes worn with normal sweatpants, how about an awesome pair of gold sneakers? Anyone wearing these is bound to be the most popular parent at the neighborhood playground.

Finally, I know Emily likes vintage styles, so I chose a pair of Warby Parker sunglasses. They excel at mixing modern with vintage. Add a warm down anorak and this casual, comfy look is complete.

A NIGHT OUT

Emily could also dress these joggers up more for a night out. Generally, I don't like the idea of wearing heels with pants like these because, in the end, you're still wearing heels with sweatpants and it looks a little odd. However, I will never say no to pairing heeled ankle boots with anything.

Add a sparkly shirt and red lipstick (I think a dark plum like this NARS Audacious Lipstick in Charlotte would look amazing on Emily), and you're dressed up just enough.

As for outerwear, I know Emily has a leopard-print coat that would also add a lot of fun (and warmth) to this outfit.

You won't be fooling anyone in a law firm with these pants, but a half-tucked button-down, oversize black blazer, and menswear-style shoes will be enough to offset their casual vibe for most artsy or relaxed offices.

Add a big-ass watch, maybe some red lipstick and bold glasses, and Emily will look like the coolest editor in New York.

If you have any suggestions for Emily on how to wear these joggers, please feel free to contribute in the comments! And if you want me to tackle your style dilemmas, post a question (with a picture if you'd like!) in the comments, too, to be considered for a future post.